N-tert-butyloxycarbonyl-alanyl-alanyl-proline | 63769-98-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butyloxycarbonyl-alanyl-alanyl-proline
• 英文别名: Boc-L-Ala-L-Ala-L-Pro；Boc-Ala-Ala-Pro-OH；Boc-(L)-AlaAlaPro-OH；Boc-AlaAlaPro-OH；Boc-L-alanyl-L-alanyl-L-proline；(2S)-1-[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 63769-98-2
• 化学式: C₁₆H₂₇N₃O₆
• 分子量: 357.407
• InChiKey: PSEXQIHRIIHENX-DCAQKATOSA-N

物化性质

• 沸点：
  626.2±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-alanyl-alanyl-proline 在 N-甲基吗啉 、 盐酸 、 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.75h， 生成 N-<<5-(dimethylamino)-1-naphtalenyl>sulfonyl>-L-alanyl-L-alanyl-N-<3,3,3-trifluoro-1-(1-methylethyl)-2-oxopropyl>-L-prolinamide
  参考文献：
  名称：

  Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G

  摘要：

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.

  DOI：

  10.1021/jm00163a063
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酰-L-脯氨酸 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 sodium hydroxide 为溶剂， 反应 24.0h， 生成 N-tert-butyloxycarbonyl-alanyl-alanyl-proline
  参考文献：
  名称：

  Martynov, V. F.; Leont'eva, L. I.; Sorochinskaya, E. I., Journal of general chemistry of the USSR, 1984, vol. 54, # 2, p. 384 - 388

  摘要：

  DOI：

文献信息

• Peptidase inhibitors
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05496927A1

  公开（公告）日：1996-03-05

  This invention relates to analogs of peptidase substrates in which the amide group containing the scissile amide bond of the substrate peptide has been replaced by an activated electrophilic ketone moiety. These analogs of the peptidase substrates provide specific enzyme inhibitors for a variety of proteases, the inhibition of which will have useful physiological consequences in a variety of disease states.

  这项发明涉及肽酶底物的类似物，其中底物肽的含有可切割酰胺键的酰胺基团已被活化的亲电酮基团所取代。这些肽酶底物的类似物为各种蛋白酶提供特异性酶抑制剂，抑制这些蛋白酶将在各种疾病状态下产生有用的生理后果。
• Synthesis and application of MeOSuc-Ala-Ala-Pro-Phe-CH2Cl as potent proteinase K inhibitor
  作者：Anilkumar R. Kore、Muthian Shanmugasundaram、Quoc Hoang、Mack Kuo、Laura M. Chapman、Helen H. Chen

  DOI：10.1016/j.bmcl.2009.01.077

  日期：2009.3

  The synthesis and proteolytic inhibitor function of two new tetrapeptides, methoxysuccinyl-Ala-Ala-Pro-Phe-chloromethyl ketone (MeOSuc-AAPF-CH2Cl) and methoxysuccinyl-Ala-Pro-Ala-Phe-chloromethyl ketone (MeOSuc-APAF-CH2Cl) are described. The efficacy of these two new analogs in inhibiting the proteolytic activity of proteinase K has been compared with the previously-documented proteainase K inhibitor

  两种新四肽的合成和蛋白水解抑制剂的功能，甲氧基琥珀酰-Ala-Ala-Pro-苯丙氨酸-氯甲基酮（MeOSuc-AAPF-CH 2 Cl）和甲氧基琥珀酰-Ala-Pro-Ala-苯丙氨酸-氯甲基酮（MeOSuc-APAF-描述了CH 2 Cl）。已经将这两种新的类似物在抑制蛋白酶K的蛋白水解活性方面的功效与先前记录的蛋白酶蛋白酶K抑制剂，甲氧基琥珀酰-Ala-Ala-Pro-Val-氯甲基酮（MeOSuc-AAPV-CH 2 Cl）进行了比较。在蛋白酶K存在下使用实时逆转录聚合酶链反应（RT-PCR）分析检测抑制活性发现，AAPF抑制剂（MeOSuc-AAPF-CH 2浓度为0.05 mM的Cl）可在30个周期（即Ct = 30）获得外源靶标（“ Xeno RNA”）的信号，而MeOSuc-AAPV-CH 2 Cl对照则需要高10倍浓度（0.5 mM）以产生相同的Ct。有趣的是，另一个新的
• Proteinase K inhibitors, methods and compositions therefor
  申请人：Life Technologies Corporation

  公开号：EP2955233A1

  公开（公告）日：2015-12-16

  Described is a process for preparing a sample containing RNA for in situ analysis using a alkoxysuccinyl-peptidyl-haloalkyl ketone to inactivate proteinase K at substantially the same temperature as for the lysis step.

  描述了一种用烷氧基琥珀酰肽基卤代烷基酮处理样品以准备含有RNA的样品，用于原位分析，以在基本相同温度下灭活蛋白酶K，与裂解步骤相同。
• Glucocorticoids
  申请人：Schering Aktiengesellschaft

  公开号：US05616573A1

  公开（公告）日：1997-04-01

  Glucocorticoids of general formula I R--Val--O--GC (II), are described, in which O-GC is the radical of a 21-hydroxycorticoid that has an antiinflammatory action, Val represents a valine radical in the 21-position of the corticoid and R means a hydrogen atom or a hydrocarbon radical with up to 32 carbon atoms that is optionally substituted by hydroxy groups, amino groups, oxo groups and/or halogen atoms and/or interrupted by oxygen atoms, SO.sub.2 groups and/or NH groups and their salts.

  描述了一般式I R--Val--O--GC(II)的糖皮质激素，其中O-GC是具有抗炎作用的21-羟基皮质激素的基团，Val代表皮质激素21位的缬氨酸基团，R表示氢原子或最多具有32个碳原子的碳氢基团，该基团可选地被羟基、氨基、氧代基和/或卤素原子取代和/或由氧原子、SO.sub.2基团和/或NH基团中断，并且它们的盐。
• Process for forming a fluoromethyl ketone
  申请人：Prototek, Inc.

  公开号：US05210272A1

  公开（公告）日：1993-05-11

  The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.

  本文介绍了制备苯甲基氟丙酸镁和其他等效材料，这些材料是--CH.sub.2 F基团的合成等效物。这些试剂与各种羧酸的原位形成的咪唑酰亚胺反应，形成β-酮-α-氟酯，经过氢化和自发脱羧反应，可以得到产率极高的氟甲基酮。因此，从RCOOH到RCOCH.sub.2 F的整个转化过程得到了说明。